When he turned in his resignation a little over a month later, the boss remembered what had happened and had both of us sit in on the interviews that she conducted for his replacement and hired the guy we were most comfortable with.

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I would find that very nerve-racking. Interviews are uncomfortable enough, but having two other people just sitting there watching me during the interview would be 10 times worse. I agree that you should spend time with those you're going to be working closely with, but perhaps a more informal setting would be better for that? You said that for your interview you spent 20 minutes sitting there chatting with a guy over coffee. That sounds much better for getting to know someone.

It's kind of funny that this is coming up now. I have a coworker and the two of us are really the only ones in our department who do the kinds of work we do. He was diagnosed with throat cancer in late February (I feel bad for him, but he also has a crappy attitude, which complicates all of this even more), and while he was supposed to return in late May, the most recent information we have is "maybe in late July". In the meantime I've had to do tasks that I've never done before and that it could be said he "casually" documented. I'm also, of course, doing the work of 1.75 people (my manager's helping me but there's a bunch of stuff he also doesn't know how to do).

Anyway, even in a best case scenario if/when my coworker returns, this seems like a rather pointed reminder that he's not going to be with the company forever. Given that the only other person familiar with what he does is me, I've idly wondered whether, if and when we look to replace him (or possibly add another person to our area) I'll be invited to sit in on the interviews, and whether I'd play an active role or would just be listening in and offering my feedback after the fact. Ironically, while I've often played a part in training new employees, I don't consider myself very patient, very tactful or much of a people person, so if there was an interview going on I'd probably be as nervous as the interviewee. Okay, not really, but you get my meaning...

If the person isn't ready for it (and it usually gets them off guard, as one usually wants to praise yourself in an interview, not talk about problems you've had)... It'll show if they can think "on their feet", as well as adapt and overcome obstacles.

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What does thinking on your feet and coming up with elaborate stories on the spot have to do with performing your job? Unless you're interviewing someone to be a talk show host, you're testing a skill that's completely irrelevant for the position at hand.

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It's not about storytelling but an interviewer usually wants to see how a candidate handles himself under pressure and asking such loaded questions is one way to do it. If the person gets a halfway decent answer together he passes showing he'll not freeze up when it gets hectic and chaotic at the job (which at some point will happen).. if he passes with flying colors, i.e. stays calm, gets together well worded sentences and appears to be truthful and what he says makes sense then he scores extra bonus points.

Once you get to an interview at all, i.e. passed basic requirements such as grades, work experience and other requirements interviewers want to get to know the person behind the diplomas, certificates and numbers and they do like to put people outside their comfort zone because it's then that most people show their true colors.

It's not about storytelling but an interviewer usually wants to see how a candidate handles himself under pressure and asking such loaded questions is one way to do it.

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I disagree with the assumption that asking loaded questions properly assesses someone's ability to handle a position where they are under pressure. It assesses your ability to do improv, but that's it. Someone can be extremely good at handling job related pressure, but shut down when asked to verbally answer a random question. The ability to think on your feet socially is very different from the ability to handle a tight deadline as an accountant.

I'm not sure I'd consider loaded questions to be without value, but I will say at my job I wish I could tell people in advance, "If you want an okay, fast answer, call me. If you want the best, most well-considered answer, email me." I hate phonecalls precisely because I don't have time to think about whatever situation I'm giving feedback on, and it seems like the callers don't appreciate the value of letting me actually think about the problem first.